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643-12-9

643-12-9 Structure

643-12-9 Structure
IdentificationMore
[Name]

D-(+)-CHIRO-INOSITOL
[CAS]

643-12-9
[Synonyms]

1D-CHIRO-INOSITOL
D-(+)-CHIRO-INOSITOL
D-CHIRO-INOSITOL
D-(+)-CHIRO-INOSITOL, 95% (96% EE/GLC)
(1R)-Cyclohexane-1r,2c,3t,4c,5t,6t-hexaol
1,2,4/3,5,6-hexahydroxycyclohexane
D-CHIRO-INOSITOL(DISD)
chiro-Inositol
D-Inositol
[EINECS(EC#)]

211-394-0
[Molecular Formula]

C6H12O6
[MDL Number]

MFCD00272608
[Molecular Weight]

180.16
[MOL File]

643-12-9.mol
Chemical PropertiesBack Directory
[Appearance]

Off-White Powder
[Melting point ]

230 °C
[Boiling point ]

232.96°C (rough estimate)
[density ]

1.2805 (rough estimate)
[refractive index ]

1.5730 (estimate)
[storage temp. ]

Freezer
[solubility ]

Water
[form ]

Solid
[pka]

12.63±0.70(Predicted)
[color ]

White to Off-White
[Optical Rotation]

[α]23/D +60°, c = 1.2 in H2O
[Water Solubility ]

403.4g/L(11 ºC)
[InChI]

InChI=1S/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5+,6+/m0/s1
[InChIKey]

CDAISMWEOUEBRE-LKPKBOIGSA-N
[SMILES]

O[C@H]1[C@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1O
[CAS DataBase Reference]

643-12-9(CAS DataBase Reference)
Questions And AnswerBack Directory
[Preparation]

D-chiro-inositol, in its pure form, is a white powder, slightly sweet, and readily soluble in water. Currently, the main method for industrial-scale production is natural extraction. D-chiro-inositol exists in nature as compounds in plants such as legumes and buckwheat, as well as insects (see Table 1). Its precursor, pinol, is also found in various plants, such as bougainvillea, sugar pine, and red sandalwood. Chemical synthesis of chiral inositol has not yet achieved a breakthrough, as the process is cumbersome and costly. Genetic engineering production of D-chiro-inositol involves genetically modifying Bacillus subtilis to convert muscle inositol into D-chiro-inositol; however, this method currently suffers from low bioconversion rates and high costs. The antibiotic kasugamycin, as a precursor of D-chiro-inositol, can be purified after acetylation, representing another production route.
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

3
[HS Code ]

29061320
Hazard InformationBack Directory
[Chemical Properties]

Off-White Powder
[Uses]

The inositols and their phosphates have been used in the development of metabolically stable insulin mediators, inhibitors, and modulators of important metabolic functions such as glycolysis. Inositols are stable to degradative enzymes in vivo because they lack a hydrolytically labile glycosidic linkage.
[Definition]

ChEBI: Myo-inositol is an inositol having myo- configuration. It has a role as a member of compatible osmolytes, a nutrient, an EC 3.1.4.11 (phosphoinositide phospholipase C) inhibitor, a human metabolite, a Daphnia magna metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite.
[Biochem/physiol Actions]

Important second messenger in insulin signal transduction.
[storage]

Store at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

D-chiro-inositol(643-12-9)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

D-chiro-Inositol(643-12-9)
[Sigma Aldrich]

643-12-9(sigmaaldrich)
[TCI AMERICA]

1D-chiro-Inositol,>98.0%(LC)(643-12-9)
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